Controller - AI-Driven Finance Leader (Remote + Equity)

Trust & Will; California City (CA); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

PTO and holidays

Excellent health benefits

Learning & development reimbursement

Remote-first environment

Job summary

Trust & Will, a remote-first digital estate planning platform, seeks a seasoned Controller to lead accounting operations for its growth phase. You will drive month-end close, tax compliance, internal controls, and audits while shaping the evolving finance tech stack.

The ideal candidate has 10+ years in accounting with leadership in high-growth settings, plus hands-on AI automation experience and familiarity with startups and IPO readiness.

Qualifications

• 10+ years in accounting with 4–5 years in a Controller role in high-growth settings.
• CPA certification preferred and strong track record in reporting and compliance.
• Hands-on AI/automation experience in accounting workflows.
• Experience designing internal controls for automated/AI-assisted processes.
• Proficient in Ramp, Rillet, Google Sheets and Excel.
• Experience with startups/IPO-related regulations and managing direct reports.

Responsibilities

• Own accounting for Trust & Will and subsidiaries; manage month-end close and tax compliance.
• Develop and maintain internal controls to scale operations.
• Lead audits and reconciliations with precision.
• Manage accounting technology stack; collaborate with FP&A for integrated systems.
• Partner with CFO on cost analysis, budgeting and strategic planning.
• Oversee vendor relationships and policy compliance.

Skills

Leadership in accounting

AI automation in accounting

Financial analysis

Communication

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning platform, seeks a seasoned Controller to lead accounting operations for its growth phase. You will drive month-end close, tax compliance, internal controls, and audits while shaping the evolving finance tech stack.

The ideal candidate has 10+ years in accounting with leadership in high-growth settings, plus hands-on AI automation experience and familiarity with startups and IPO readiness.